I did an earlier piece published in TG Forum on Do You Think I’m Sexy which talked to the crossdresser’s self image of sexy which is not necessary flattering. But achieving that sexy look without wearing mini-skirts, double-D boobs, or skin tight clothing can be achieved by following some of these practices from Cynthis Nellis at About.com.
Wear Something in an Unexpected Way
It doesn’t have to be a huge statement like wearing a jacket backwards; subtle alterations pack the chicest punch. For example, take a basic man’s white shirt (slightly oversized), unbutton it, wrap it so that one side overlaps the over and tuck in.) If you collect these useful hints in a notebook, you’ll have a real start in creating a different look…being individualistic, like real women do.
Another way to look sexy is to take a cue from Scarlett Johansson and wear menswear. A tuxedo on a woman — either worn literally with a shirt and bowtie or with a feminine cami — is super sexy.
Wear Red Lipstick
Pale lips may be trendy, but nothing does the job like red. This is my very favorite tip as nothing is quite as striking as red lips. Use lipliner for a perfect appearance, choose a creamy matte in a red that best suits your skin tone (blue-reds for darker skin tones; orangey hues for olive; true reds for blondes). Use a light hand for the rest of the face because the lips should take center stage. Over 40, beware harsh reds because they can look too stark on your mature skin.
Wear a Hat
Nothing attracts attention quite like a hat. First, it takes guts to wear one. Second, it takes panache to carry it off. Combine the two qualities and you get major sex appeal. Stay with classic shapes — the fedora, the beret — to make it easier to pull off. No one pulls off hats better than the British and Kate Middleton has ushered in a new era for hats for women around the globe.
Accessorize with Shoulder-Duster Earrings
Skip every other piece of jewelry, pull your hair back and make sure your makeup stays soft. This look goes great with bare shoulders and updos, too. Definitely an after-dark look. Long, bold earrings look gorgeous with short hair and updos. Now I know crossdressers love their long hair, but nothing is quite as glamorous as an updo. Here’s how to do one or have your hairstylist show you how. It’s worth the effort.
Make It Metallic
Gold, silver, copper and pewter are especially luminous when you’re going for vavoom. Look for simple shapes (the story here is the fabric and color, not the line of the outfit) and tones that flatter your skin color. Pass on major jewelry and makeup to let the metallics shine. You can even use metallics in your makeup alone, by opting for shimmery eyeshadows (but be cautious if you are over a certain age) or bronzers for a golden glow.
Adopt an Exotic Look
Harem pants, sarongs and embroidered items are all borrowed ethnic looks with tons of feminine charm. The mandarin-collar dress (cheongsam) from China is flattering, chic and always intriguing. The idea is richness and ornamentation to create an exotic, sexy look.
Perhaps the single sexiest item you can own are a great pair of sunglasses. They add tons of mystery, look cute even on top of your head and actually serve the practical purpose of protecting your eyes. And, yes, you can wear them indoors when you want to make a major fashion statement.
Stay Soft with Touchable Fabrics
Forget everything you’ve ever heard about hardcore leathers or sparkly sequins being heat-inducing. Cashmere, silky satin, buttery soft suedes are the real scene-stealers. Touchable fabrics not only invite another’s touch, they have the added bonus of feeling great against your skin so you feel pampered and sexy.
No need to bare your breasts, even with lace. Nude linings, camisoles and slips all keep you covered while the lace itself stays really suggestive. Even lace trims add a sexy, alluring look to everything from a simple jacket to a black skirt. Cutouts are another way to show slivers of sexy skin without baring it all.